The main character is Seamus O'Neill, played by Fisher Stevens, a factory worker from New Jersey who dreams of being a writer.

When he wins the lottery, he uses his newfound wealth to move to Key West to pursue his writing career, where his idol Ernest Hemingway had lived.

This brings him into conflict with the paper's editor, Roosevelt Cole (Ivory Ocean), who remarks "You want to report on the Spanish Civil War?"

In a later episode it was revealed Seamus is once again poor as his lottery winnings were seized due to taxation and multiple unpaid debts, and it will be several years before his next annuity check resumes.

In addition to Stevens, Jennifer Tilly, Denise Crosby, and Brian Thompson led the large ensemble cast as the town's high-class prostitute, conservative mayor and eccentric sheriff, respectively.